5-Amino-2-naphthalenesulfonic acid supplier

Name
1-Aminonaphthalene-6-sulfonic acid
EINECS 204-351-2
CAS No. 119-79-9
Article Data12
CAS DataBase
Density 1.502 g/cm³
Solubility 1g/L(16 oC)
Melting Point >300 °C
Formula C₁₀H₉NO₃S
Boiling Point
Molecular Weight 223.252
Flash Point
Transport Information UN 1759
Appearance grey-red power
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols R36/37/38:Irritating to eyes, respiratory system and skin.;
Synonyms 1,6-Cleve'sacid;1-Amino-6-naphthalenesulfonic acid;1-Amino-6-sulfonaphthalene;1-Naphthylamine-6-sulfonic acid;5-Amino-2-nanphthalenesulfonic acid;5-Naphthylamine-2-sulfonic acid;6-Sulfo-1-naphthylamine;Cleve's acid;Cleve's b-acid;NSC 31506;NSC 4984;1,6-cleve's acid;2-naphthalenesulfonic acid, 5-amino-;5-Aminonaphthalene-2-sulfonic acid;5-Ammonionaphthalene-2-sulfonate;
PSA 88.77000
LogP 3.33070

Synthetic route

: 120-18-3
naphthalene-2-sulfonate

A: 119-79-9
5-aminonaphthalene-2-sulfonic acid

B: 119-28-8
8-amino-2-naphthalenesulfonic acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 25℃; anschl. bei 10grad, Reduzieren des erhaltenen Gemisches mit Eisen und sehr verd. Salzsaeure;
With sulfuric acid; nitric acid at 25℃; dann bei 10grad, Reduzieren des erhaltenen Gemisches mit Eisen und sehr verd. Salzsaeure;
Stage #1: naphthalene-2-sulfonate With sulfuric acid at 120℃; for 0.666667h; Stage #2: With nitric acid at 33 - 35℃; for 20h; Reagent/catalyst; Overall yield = 86 percent; Overall yield = 75 g; Further stages;

: 86-69-1
1-nitro-6-naphthalenesulfonic acid

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With ammonium sulfide
With iron; acetic acid

: 134-32-7
1-amino-naphthalene

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With sulfuric acid at 125 - 130℃;

: 7664-93-9
sulfuric acid

: 134-32-7
1-amino-naphthalene

A: 119-79-9
5-aminonaphthalene-2-sulfonic acid

B: 84-89-9
1-aminonaphthalene-5-sulfonic acid

Conditions

Conditions	Yield
at 125 - 130℃; bei laengerem Erhitzen;

...Expand

: 7664-93-9
sulfuric acid

: 134-32-7
1-amino-naphthalene

A: 119-79-9
5-aminonaphthalene-2-sulfonic acid

B: 84-89-9
1-aminonaphthalene-5-sulfonic acid

C: 85-75-6
4-aminonaphthalene-1,6-disulfonic acid

Conditions

Conditions	Yield
at 125 - 130℃; bei laengerem Erhitzen;

...Expand

: 84-86-6
4-amino-1-naphthalenesufonic acid

: 7664-93-9
sulfuric acid

A: 119-79-9
5-aminonaphthalene-2-sulfonic acid

B: 84-89-9
1-aminonaphthalene-5-sulfonic acid

C: 85-75-6
4-aminonaphthalene-1,6-disulfonic acid

Conditions

Conditions	Yield
at 125 - 130℃;

...Expand

: 86-69-1
1-nitro-6-naphthalenesulfonic acid

ammonium sulfide: ammonium sulfide

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 121-90-4
m-nitrobenzoic acid chloride

: 5-(3-nitrobenzamido)naphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With sodium carbonate In water; toluene pH=5;	96%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

poly(5-aminonaphthalene-2-sulphonic acid): poly(5-aminonaphthalene-2-sulphonic acid)

Conditions

Conditions	Yield
With sodium hydroxide; sodium periodate; aniline hydrochloride In water oxidative polymerization;	95%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 24424-99-5
di-tert-butyl dicarbonate

: 1415094-45-9
5-(tert-butoxycarbonylamino)naphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃; Inert atmosphere;	94%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 98-88-4
benzoyl chloride

: 5-benzamidonaphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With sodium carbonate In water; toluene pH=5;	94%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 123-54-6
acetylacetone

: 4-hydroxy-3-(6'-sulfonyl-1'-azonaphthyl)-3-penten-2-one

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite In water for 0.5h; Stage #2: acetylacetone With sodium carbonate In water for 0.5h; pH=7; Further stages.;	93%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 99-98-9
4-amino-N,N-dimethylaniline

: acide 5[(2'-acide sulfonique-5'-aminonaphthalenyl)imino]-8-(N,N-dimethyl-p-aminophenyl)iminonaphthalene-2-sulfonique

Conditions

Conditions	Yield
With ammonium peroxydisulfate; acetic acid; triethylamine In methanol; water at 0℃; for 3h; Condensation;	90%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 776325-74-7
4-hydroxy-1-(4-sulphophenyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

: 5-(6'-sulphonaphthyl)azo-1-(4'-sulphophenyl)-4-hydroxy-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite at 0 - 5℃; for 3h; Stage #2: 4-hydroxy-1-(4-sulphophenyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole With sodium carbonate for 3.5h;	86%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 776325-76-9
4-hydroxy-1-(2',5'-dichloro-4'-sulphophenyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

: 5-(6'-sulphonaphthyl)azo-1-(2',5'-dichloro-4'-sulphophenyl)-4-hydroxy-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite at 0 - 5℃; for 3h; Stage #2: 4-hydroxy-1-(2',5'-dichloro-4'-sulphophenyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole With sodium carbonate	86%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 776325-78-1
4-hydroxy-1-(6'-sulphonaphtyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

: 5-(6'-sulphonaphthyl)azo-1-(6'-sulphonaphthyl)-4-hydroxy-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite at 0 - 5℃; for 3h; Stage #2: 4-hydroxy-1-(6'-sulphonaphtyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole With sodium carbonate	86%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 776325-77-0
4-hydroxy-1-(8'-sulphonaphtyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

: 5-(6'-sulphonaphthyl)azo-1-(8'-sulphonaphthyl)-4-hydroxy-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite at 0 - 5℃; for 3h; Stage #2: 4-hydroxy-1-(8'-sulphonaphtyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole With sodium carbonate	85%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 776325-75-8
4-hydroxy-1-(2'-carboxy-4'-sulphophenyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

: 5-(6'-sulphonaphthyl)azo-1-(2'-carboxy-4'-sulphophenyl)-4-hydroxy-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite at 0 - 5℃; for 3h; Stage #2: 4-hydroxy-1-(2'-carboxy-4'-sulphophenyl)-3-[N-(2'-oxobenzimidazol-5'-yl)carboxamide]pyrazole With sodium carbonate	85%

: 110-86-1
pyridine

: 81-84-5
1,8-Naphthalic anhydride

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C22H13NO5S*C5H5N

Conditions

Conditions	Yield
for 8h; Reflux;	81%

...Expand

: 74124-79-1
di(succinimido) carbonate

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 1178554-82-9
5-amino-2-naphthalenesulfonic acid-N-hydroxysuccinimidyl carbamate

Conditions

Conditions	Yield
In acetonitrile Reflux;	80%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 122-04-3
4-nitro-benzoyl chloride

: C17H11N2O6S(1-)*Na(1+)

Conditions

Conditions	Yield
With sodium carbonate In water; toluene at 20℃; for 12h; pH=4;	80%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 99-98-9
4-amino-N,N-dimethylaniline

: acide 7-[(N,N-dimethyl-p-aminophenyl)amino]-8-[(N,N-dimethyl-p-aminophenyl)imino]-5-iminonaphthalene-2-sulfonique

Conditions

Conditions	Yield
With ammonium peroxydisulfate In dimethyl sulfoxide at 20℃; for 5h; oxidative condensation;	75%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 874-60-2
4-methyl-benzoyl chloride

: 5-(4-methylbenzamido)naphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With sodium carbonate In water; toluene pH=5;	74%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 776325-68-9
4-bromo-3-oxo-N-(2'-oxobenzimidazol-5'-yl)butyramide

: 5-{N'-[3-bromo-2-oxo-1-(2-oxo-2,3-dihydro-1H-benzoimidazol-5-ylcarbamoyl)-propylidene]-hydrazino}-naphthalene-2-sulfonic acid

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite for 0.416667h; cooling; Stage #2: 4-bromo-3-oxo-N-(2'-oxobenzimidazol-5'-yl)butyramide With sodium hydroxide at 0 - 3℃;	73%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 99-63-8
benzene-1,3-dicarbonyl dichloride

: disodium 5,5'-[1,3-phenylenebis(carbonylimino)]bis-2-naphthalenesulfonate

Conditions

Conditions	Yield
With sodium carbonate In chloroform; water at 25℃; for 16h;	72%

: C25H20N4O4S

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C35H26N6O7S2

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite Stage #2: C25H20N4O4S With sodium hydroxide at 0 - 3℃; Further stages.;	71%

: C24H18N4O3S

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C34H24N6O6S2

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite Stage #2: C24H18N4O3S With sodium hydroxide at 0 - 3℃; Further stages.;	70%

: C24H17N5O5S

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C34H23N7O8S2

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite Stage #2: C24H17N5O5S With sodium hydroxide at 0 - 3℃; Further stages.;	70%

: 2-(4'-oxo-2'-phenyl-1',3'-thiazol-3'-yl)-3-[α-(p-carbethoxyphenylhydrazono)phenoxymethyl]-1,2,4-benzothiadiazine 1,1-dioxide

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C42H33N7O9S3

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite for 0.416667h; cooling; Stage #2: 2-(4'-oxo-2'-phenyl-1',3'-thiazol-3'-yl)-3-[α-(p-carbethoxyphenylhydrazono)phenoxymethyl]-1,2,4-benzothiadiazine 1,1-dioxide With sodium hydroxide at 0 - 3℃; for 0.166667h;	69%

: C24H19N5O3S

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C34H25N7O6S2

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite Stage #2: C24H19N5O3S With sodium hydroxide at 0 - 3℃; Further stages.;	69%

: 2-(4'-oxo-3'-phenyl-1',3'-thiazol-2'-ylimino)-3-[α-(p-tolylhydrazono)phenoxymethyl]-1,2,4-benzothiadiazine 1,1-dioxide

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C40H30N8O7S3

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite for 0.416667h; cooling; Stage #2: 2-(4'-oxo-3'-phenyl-1',3'-thiazol-2'-ylimino)-3-[α-(p-tolylhydrazono)phenoxymethyl]-1,2,4-benzothiadiazine 1,1-dioxide With sodium hydroxide at 0 - 3℃; for 0.166667h;	61%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 1218759-53-5
N,N’-(dimethylethylenediaminothiosemicarbazanato)-4-(methylthiosemicarbazanato)butane-2,3-diimine

: 1229570-75-5
C2H7N*C17H20N6O3S3

Conditions

Conditions	Yield
In acetonitrile Reflux; Inert atmosphere;	61%

: C30H22N6O6S2

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C50H34N10O12S4

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite Stage #2: C30H22N6O6S2 With sodium hydroxide at 0 - 3℃; Further stages.;	60%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 5-bromonaphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With urea; sodium nitrite; copper(I) bromide In sodium hydroxide; water; hydrogen bromide	57%
With urea; sodium nitrite; copper(I) bromide In sodium hydroxide; water; hydrogen bromide	57%
With urea; sodium nitrite; copper(I) bromide In sodium hydroxide; water; hydrogen bromide	57%
With urea; sodium nitrite; copper(I) bromide In sodium hydroxide; water; hydrogen bromide	57%
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogen bromide; sodium hydroxide; sodium nitrite In water at -5 - 2℃; for 0.833333h; Stage #2: With hydrogen bromide; copper(I) bromide In water at 80℃; for 0.5h;	6.16 g

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

sodium 1,2-naphthoquinone-4-sulfonate: sodium 1,2-naphthoquinone-4-sulfonate

: 724743-88-8
5-((3,4-dioxo-3,4-dihydronaphthalen-1-yl)amino)naphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With potassium carbonate In water	56.6%

: C28H20N6O5S2

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: C48H32N10O11S4

Conditions

Conditions	Yield
Stage #1: 5-aminonaphthalene-2-sulfonic acid With hydrogenchloride; sodium carbonate; sodium nitrite Stage #2: C28H20N6O5S2 With sodium hydroxide at 0 - 3℃; Further stages.;	53%

: 119-79-9
5-aminonaphthalene-2-sulfonic acid

: 10397-30-5
4-methyl-3-nitrobenzoyl chloride

: 5-(4-methyl-3-nitrobenzamido)naphthalene-2-sulfonic acid

Conditions

Conditions	Yield
With sodium carbonate In water; toluene pH=5;	47%

5-Amino-2-naphthalenesulfonic acid Consensus Reports

Reported in EPA TSCA Inventory.

5-Amino-2-naphthalenesulfonic acid Specification

The 5-Amino-2-naphthalenesulfonic acid, with the CAS registry number 119-79-9 and EINECS registry number 257-269-4, has the systematic name of 5-aminonaphthalene-2-sulfonic acid. It is also known as 1,6-cleve's acid. And the molecular formula of this chemical is C₁₀H₉NO₃S. It belongs to the following product categories: Intermediates of Dyes and Pigments; Organics; Organic Building Blocks; Sulfonic/Sulfinic Acids; Sulfur Compounds.

The physical properties of 5-Amino-2-naphthalenesulfonic acid are as following: (1)ACD/LogP: 0.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.03 ; (4) ACD/LogD (pH 7.4): -3.08; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 54.99 Å²; (13)Index of Refraction: 1.713; (14)Molar Refractivity: 58.27 cm³; (15)Molar Volume: 148.6 cm³; (16)Polarizability: 23.1×10^-24cm³; (17)Surface Tension: 72.1 dyne/cm; (18)Density: 1.502 g/cm³.

Preparation and uses of 5-Amino-2-naphthalenesulfonic acid(1,6-cleve's acid): It can start with the sulfonation of refined naphthalene, and gives 2-naphthalene sulfonic acid. The nitrification of 2-naphthalene sulfonic acid gives mixture of 1-nitro-6-naphthalene sulfonic acid and 1-nitro-7- naphthalene sulfonate. After the reduction of the mixture with magnesium salts, you can get magnesium aminonaphthol sulfonic acid. Seperate the mixture by taking advantage of difference solubility in a certain temperature. Then the desired 1,6-cleve's acid is obtained, and the other product is 1,7-cleve's acid. What's more, it is used in the preparation of azo dyes and sulfur dyes, such as direct fast blue BGL and sulfur blue CV.

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(O)c1ccc2c(c1)cccc2N
(2)InChI: InChI=1/C10H9NO3S/c11-10-3-1-2-7-6-8(15(12,13)14)4-5-9(7)10/h1-6H,11H2,(H,12,13,14)
(3)InChIKey: UWPJYQYRSWYIGZ-UHFFFAOYAF

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	14200mg/kg (14200mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1056, 1986.

Product Name

1-Aminonaphthalene-6-sulfonic acid

Synthetic route

5-Amino-2-naphthalenesulfonic acid Consensus Reports

5-Amino-2-naphthalenesulfonic acid Specification

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